30-O-methyl spergulagenate | 25488-57-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 30-O-methyl spergulagenate
• 英文别名: 30-methylspergulagenate；serjanic acid；Methyl-Spergulagenat；Methylspergulagenat；Serjansaeure；(2S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2-methoxycarbonyl-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 25488-57-7
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: BZXSGMYHHGCPEN-RUUKHNDOSA-N

物化性质

• 熔点：
  230-235 °C(Solv: methanol (67-56-1))
• 沸点：
  588.1±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  30-O-methyl spergulagenate 在 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 queretarol
  参考文献：
  名称：

  Steroids and triterpenoids from the roots of Mollugo spergula

  摘要：

  DOI：

  10.1016/s0031-9422(00)94708-3
• 作为产物：
  描述：

  (3β)-3-acetoxy-30-methoxy-30-oxo-olean-12-en-28-oic acid 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以45 mg的产率得到30-O-methyl spergulagenate
  参考文献：
  名称：

  来自商陆的三萜类化合物，三种齐墩果烷衍生物

  摘要：

  摘要 除了30-甲基精草酸盐外，还从商陆脱脂浆果的酒精提取物中分离并表征了三种新的齐墩果烷衍生物，即spergulagenic acid A、isophytolaccinic acid A和isophytolaccagenin A。新化合物已被鉴定为3β-乙酰氧基-30β-methyloleanate-12-en-28β-oic acid；3β,23α-diacetoxy-28β-methyloleanate-12-en-30β-oic 酸和 2β, 3β,23α-triacetoxy-28β-methyloleanate-12-en-30β-oic 酸，分别。

  DOI：

  10.1016/s0031-9422(00)80274-5

文献信息

• Molluscicidal saponins from Phytolacca icosandra
  作者：Virginie Treyvaud、Andrew Marston、Wahyo Dyatmiko、Kurt Hostettmann

  DOI：10.1016/s0031-9422(00)00233-8

  日期：2000.11

  Five monodesmosidic serjanic acid saponins and a monodesmosidic spergulagenic acid saponin were isolated from an aqueous extract of the berries of Phytolacca icosandra. A methanol extract of the berries furnished three bidesmosidic serjanic acid glycosides. Their structures were established by spectroscopic (ES-MS, 1H NMR, COSY, HSQC, HMBC, 13C NMR) and chemical methods. The molluscicidal, spermicidal

  从 Phytolacca icOSandra 浆果的水提取物中分离出五种单链丝氨酸皂苷和一种单链丝木霉酸皂苷。浆果的甲醇提取物提供了三种双糖苷 serjanic 酸苷。它们的结构是通过光谱（ES-MS、1H NMR、COSY、HSQC、HMBC、13C NMR）和化学方法确定的。研究了皂苷的杀软体动物、杀精子和溶血特性。
• Photochemical transformation leading to eupteleogenin—II
  作者：I. Kitagawa、K. Kitazawa、K. Aoyama、M. Asanuma、I. Yosioka

  DOI：10.1016/0040-4020(72)80150-9

  日期：——

  As a continuation of the preceding paper, to search for the photochemical means to induce a terminal methylene moiety, which is another unique function of eupteleogenin (1a), photolysis of leucotylic acid derivatives (2a-d) has been pursued as the model experiment. Although the aimed terminal methylene compound (3a) was obtained, the method has been found inapplicable for decarboxylation of 7a, b.

  作为前一篇论文的续篇，为寻找诱导末端亚甲基部分的光化学方法（这是正肽原蛋白（1a）的另一个独特功能），已尝试将白果酸衍生物（2a-d）进行光解作为模型实验。尽管获得了目标的末端亚甲基化合物（3a），但是发现该方法不适用于7a，b的脱羧。基于本论文和先前论文的综合证据，已完成了将产精酸衍生物（5a，b）转化为乙酸正庚原素（1b），其中通过四乙酸铅氧化实现了7b的脱羧。
• Synthesis of ring-A serjanic acid derivatives and their cytotoxic evaluation through the brine shrimp lethality assay (BSLA)
  作者：Elier Galarraga、Sherezade Gómez、Andersson Mavares、Neudo Urdaneta、Juan Manuel Amaro-Luis

  DOI：10.1515/znb-2022-0064

  日期：2022.9.27

  benzaldehydes 16–23, afforded benzylidine ketones 24–31. All compounds were elucidated on the basis of NMR and HR-MS spectroscopic data and evaluated for their in-vitro cytotoxicity to the Brine Shrimp Lethality Assay (BSLA). As a result, the compounds exhibited medium to good cytotoxic potential and this activity was as high as eight times that of serjanic acid (1) on the tested zoophytes.

  通过对三萜骨架的 A 环进行修饰，合成了 16 种serjanic 酸衍生物。中间体 2 与必要的芳香族肼的 Fischer 吲哚化得到吲哚三萜 8-13。此外，2 与盐酸羟胺在吡啶中的反应提供了所需的 C-3 肟 14，而吡嗪 15 通过 2 在乙二胺和硫的存在下在吗啉中缩合获得。最后，中间体 2 与相应的取代苯甲醛 16-23 进行 CLAisen-Schmidt 缩合，得到苄叉酮 24-31。所有化合物均在 NMR 和 HR-MS 光谱数据的基础上进行了鉴定，并对其进行了评估体外对盐水虾致死率测定 (BSLA) 的细胞毒性。结果，这些化合物表现出中等至良好的细胞毒性潜力，并且这种活性对测试的动植物而言是丝氨酸 (1) 的八倍。
• Polynucleotide binding complexes comprising sterols and saponin
  申请人：Nordic Vaccine Technology A/S

  公开号：EP2011517A1

  公开（公告）日：2009-01-07

  The present invention pertains to complexes comprising sterols and saponins. The complexes are capable of binding a genetic determinant including a polynucleotide. The complexes may further comprise a lipophilic moiety, optionally a lipophilic moiety comprising a contacting group and/or a targeting ligand, and/or a saccharide moiety. The complexes may further comprise an immunogenic determinant and/or an antigenic determinant and/or a medicament and/or a diagnostic compound. The complexes may in even further embodiments be encapsulated by an encapsulation agent including a biodegradable microsphere. The present invention also pertains to pharmaceutical compositions and methods of treatment of an individual by therapy and/or surgery, methods of cosmetic treatment, and diagnostic methods practised on the human or animal body.

  本发明涉及由甾醇和皂甙组成的复合物。这些复合物能够结合包括多核苷酸在内的遗传决定因子。复合物可进一步包含亲脂分子，可选择包含接触基团和/或靶向配体的亲脂分子和/或糖分子。复合物可进一步包括免疫原决定簇和/或抗原决定簇和/或药物和/或诊断化合物。在更进一步的实施方案中，复合物可被包括生物可降解微球在内的封装剂封装。本发明还涉及通过治疗和/或手术对个体进行治疗的药物组合物和方法、美容治疗方法以及对人体或动物体进行诊断的方法。
• Triterpenoids with antimicrobial activity from Drypetes inaequalis
  作者：Simon Suh Awanchiri、Hanh Trinh-Van-Dufat、Jovita Chi Shirri、Marlise Diane J. Dongfack、Guy Merlin Nguenang、Sabrina Boutefnouchet、Zacharias T. Fomum、Elisabeth Seguin、Philippe Verite、François Tillequin、Jean Wandji

  DOI：10.1016/j.phytochem.2008.12.017

  日期：2009.2

  The air-dried stems and ripe fruit of Drypetes inaequalis Hutch. (Euphorbiaceae) were studied. Four triterpene derivatives, characterized as lup-20(29)-en-3 beta,6 alpha-diol, 3 beta-acetoxylup-20(29)-en-6 alpha-ol. 3 beta-caffeoyloxylup-20(29)-en-6 alpha-ol and 28-beta D-glucopyranosyl-30-methyl 3 beta-hydroxyolean-12-en-28,30-dioate along with 10 known compounds were isolated from the whole stems. One triterpene. characterized as 3 alpha-hydroxyfriedelan-25-al along with six known compounds were isolated from the ripe fruit. Their structures were established on the basis of spectroscopic analysis and chemical evidence. The triterpenes were tested for antimicrobial activity against some Gram-positive and Gram-negative bacteria, and two of them appeared to be modestly active. (C) 2009 Elsevier Ltd. All rights reserved.